What happens when one privacy advocate tries to surprise another privacy advocate with a gift? No one could have foreseen what happened, right?
Regular readers of this site know how much Joe Cadillic contributes on a regular basis. When he’s not busy writing his own blog posts for his site, MassPrivateI, he’s sending me links to stories that I might want to post here, or to other news on civil liberties issues of interest to us both.
This blog has no commercial sponsorship or income, so I can’t really afford to hire help. There are a few people who donate their mad skills to help me with security and other issues on the site, but I really can’t afford to hire actual staff who would get any salary.
Anyway, this year, I was fortunate enough to earn more income than I have in past years, and I thought I’d share a bit of my good fortune with Joe. I decided to send Joe a surprise gift — a small, unrestricted grant/award for him to use to support his work on civil liberties and surveillance/privacy issues. I thought it would be a simple matter, using PayPal to send the payment to Joe’s email address.
Clearly, I thought wrong.
As the day went on and I didn’t get any email from Joe saying “Wow,” or even any acknowledgement, I began to get concerned that I had done the money-sending bit wrong. So I emailed Joe and told him to look for email from me or PayPal.
Nothing.
Hours later, Joe emailed me that he had no email from me or PayPal.
Then I remembered that the email — if it had come from me — would have been from another email address and not the one Joe would recognize.
No problem. I told Joe to just login to his PayPal account and check “Activity.”
The next thing I know, I receive an email from PayPal that Joe has refunded all the money to me.
What? WHAT?
I contacted Joe to ask him what the heck he had done.
It turns out that because Joe is so protective of his privacy and his PayPal account, he had no idea how I could have sent anything to his PayPal account, and so he hadn’t believed he was really getting money. He hadn’t read the note, and thought it was all a scam. And as he does with phishing emails or scams, he had just deleted the first email, and clicked “refund.”
My day was not going well.
I screamed at the monitor, and initiated a chat with PayPal as to how to cancel Joe’s refund of the money I had sent him.
It couldn’t be done, they said. I had to start over.
So I started over. And once again, I sent Joe some money as an unrestricted grant/award for him to use at his sole discretion.
This time, though, I added a note: “Do NOT screw this up – or else!”
Eventually, Joe received the gift and I got my refund from the first gift. Of course, even that didn’t go smoothly. Joe sent me a thank-you note via encrypted email. I couldn’t encrypt my answer to it for some reason. By that point, I no longer cared. 
So the take-home message is that one privacy advocate should probably never try to surprise another privacy advocate — especially if that privacy advocate is a very very suspicious soul.
Merry Christmas and Happy and Healthy New Year, Joe. And please keep up your great work increasing our awareness of surveillance and privacy issues.